Michael Saylor
Born 1965 · Age 61
American entrepreneur, co‑founder and executive chairman of MicroStrategy (rebranded Strategy in 2025). Longtime technology executive, inventor, author and prominent corporate Bitcoin advocate. Founder of the Saylor Foundation / Saylor Academy.
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Life & Career Timeline
Born in Lincoln, Nebraska
Michael J. Saylor was born in Lincoln, Nebraska to a U.S. Air Force family.
Family settled in Fairborn, Ohio
After moving among Air Force bases worldwide, the family settled near Wright-Patterson AFB in Fairborn, Ohio.
Joined Theta Delta Chi fraternity; met Sanju Bansal
At MIT he joined Theta Delta Chi, where he met future MicroStrategy co‑founder Sanju Bansal.
Enrolled at MIT on AFROTC scholarship
Entered the Massachusetts Institute of Technology on a full Air Force Reserve Officer Training Corps scholarship.
Graduated MIT with dual degrees (highest honors)
Earned dual degrees in Aeronautics & Astronautics and Science, Technology & Society; wrote a thesis on system dynamics.
Commissioned as Second Lieutenant & completed flight officer training
Completed flight officer training and was commissioned in the Air Force Reserve (medical issues later prevented a pilot career).
Medical disqualification from pilot program
A medical condition (benign heart murmur) prevented a career as a jet pilot, redirecting him to consulting and industry roles.
Joined The Federal Group, Inc. (consulting)
Early professional role building computer simulation models and software integration.
Internal consultant at DuPont; paid for global titanium market model
Developed computer models predicting market changes; reportedly was paid $250,000 by DuPont for a global titanium-sector model and used funds to start his company.
Founded MicroStrategy (co‑founder with Sanju Bansal)
Used simulation/analytics experience to found the business‑intelligence and analytics company MicroStrategy.
Won $10M McDonald's contract
MicroStrategy secured a $10 million contract to build analytics applications to analyze promotion efficiency for McDonald's — a transformative early customer win.
Relational OLAP / decision‑support momentum from McDonald's project
The McDonald's engagement convinced Saylor MicroStrategy could build business intelligence (R/OLAP) tools that turn corporate data into actionable insights.
MicroStrategy ranked among top DSS vendors
By 1995 MicroStrategy was one of the top decision‑support system / DSS software creators in the U.S.
Named KPMG Washington High‑Tech Entrepreneur of the Year
Received KPMG's 'Washington High‑Tech Entrepreneur of the Year' honor.
Named Ernst & Young 'Software Entrepreneur of the Year'
Received Ernst & Young recognition for entrepreneurship in software.
Red Herring listed him among Top 10 Entrepreneurs
Named one of Red Herring's 'Top 10 Entrepreneurs for 1998'.
Took MicroStrategy public (IPO)
MicroStrategy's initial public offering priced 4,000,000 shares at $12 per share (NASDAQ: MSTR); stock doubled on the first trading day.
Named MIT Technology Review 'Innovator Under 35' & founded Saylor Foundation
Recognized as an 'Innovator Under 35' and established The Saylor Foundation (later Saylor Academy) to expand access to free education.
Established Saylor Foundation (later Saylor Academy)
Founding of Saylor Foundation to support education and philanthropy; later grew the free online Saylor Academy serving millions.
Approximately two dozen class action lawsuits filed (2000)
Following the restatement and market collapse, class action securities suits were filed against MicroStrategy.
Net worth peak then collapse: early 2000 $7B then fell ~$6B
By early 2000 Saylor's net worth had been reported at about $7 billion; after the accounting restatement and stock collapse his net worth fell by roughly $6 billion.
Public attention and controversy during the dot‑com implosion
High‑profile coverage described Saylor as a central figure in the MicroStrategy crash and ensuing SEC scrutiny; he subsequently rebuilt the business.
MicroStrategy restated financial results; stock crash
MicroStrategy announced restatement of two years of financial results; the stock — which had risen from ~$7 to as high as ~$333 — plunged (a key event in the dot‑com bubble burst).
SEC filed civil charges and settlement reached
U.S. Securities and Exchange Commission filed charges (Dec 2000). MicroStrategy and executives ultimately settled; Saylor paid $350,000 in penalties plus $8.3 million in personal disgorgement without admitting wrongdoing.
Launched Saylor.org (Saylor Academy free education initiative)
Saylor.org was launched as the free education initiative of The Saylor Foundation.
Published 'The Mobile Wave: How Mobile Intelligence Will Change Everything'
Authored and published The Mobile Wave (Perseus Books) about the impact of mobile technology; later became a best seller.
The Mobile Wave ranks on Wall Street Journal best‑seller list
Reached #5 on the Wall Street Journal hardcover business best‑sellers list (July 2012).
The Mobile Wave ranks on New York Times best‑seller list
Ranked #7 on the New York Times hardcover non‑fiction best‑seller list (August 2012).
Sale of Angel.com to Genesys
Angel.com, a cloud interactive voice response company Saylor created, was sold to Genesys Telecommunications Laboratories for $110 million.
Reduced CEO cash compensation to $1
Following criticism from major investors, Saylor switched to a symbolic $1 salary (no cash bonuses) while retaining stock‑based compensation options.
Patent portfolio reported (31 patents granted + 9 applications)
As of 2016 Saylor had been granted 31 patents with nine additional patent applications under review.
Reported patent portfolio (31 granted patents, 9 applications)
By 2016 Saylor had been granted 31 patents with nine pending applications (innovation and IP milestone).
MicroStrategy purchased another $50M in Bitcoin (early Dec 2020)
Continued corporate purchases of Bitcoin as part of a steady accumulation program.
Transformed corporate strategy to use Bitcoin as treasury reserve
Saylor repositioned MicroStrategy's treasury strategy around Bitcoin accumulation — an influential corporate precedent for institutional BTC allocation.
Sent internal memo criticizing COVID countermeasures
Distributed a 3,000‑word memo to MicroStrategy employees titled 'My Thoughts on COVID‑19' criticizing social distancing measures and announcing he would not close offices unless legally required.
Announced intention to consider Bitcoin for treasury reserves
On a quarterly earnings call Saylor announced MicroStrategy would explore purchasing Bitcoin, gold, or other alternative assets instead of holding cash.
MicroStrategy purchased $250M of Bitcoin (first major buy)
MicroStrategy used $250 million of corporate cash to purchase 21,454 BTC, marking the start of its corporate Bitcoin accumulation strategy.
MicroStrategy purchased additional $175M of Bitcoin
Added $175 million more in Bitcoin acquisitions as part of the strategy to hold BTC as a treasury reserve asset.
Saylor personal Bitcoin purchase (17,732 BTC for $175M)
Reported personal acquisition of 17,732 BTC for $175 million (disclosed in 2020 filings/media coverage).
Sold $650M in convertible senior notes to buy more Bitcoin
MicroStrategy issued $650 million of convertible senior notes (debt financing) to fund additional Bitcoin purchases.
Reported holdings: 70,470 BTC ($1.125B)
MicroStrategy announced total holdings of 70,470 BTC purchased for $1.125 billion at an average price of $15,964 per bitcoin (Dec 21, 2020).
Became Executive Chairman; Phong Le named CEO
Saylor stepped down as MicroStrategy CEO and assumed the title of Executive Chairman to focus on bitcoin acquisition and advocacy; Phong Le became CEO.
DC Attorney General sued Saylor for tax fraud
The District of Columbia Attorney General sued Saylor alleging he avoided more than $25 million in D.C. taxes by misrepresenting his residency for tax years 2005–2021.
MicroStrategy sold 704 BTC (first sale)
MicroStrategy sold 704 BTC (reported Dec 22, 2022), the first sale of corporate BTC holdings, netting roughly $11.8M.
Judge dismissed portion of DC case
In March 2023 a D.C. Superior Court judge dismissed part of the Attorney General's lawsuit against Saylor and MicroStrategy; other claims were allowed to proceed.
Keynote / prediction at Bitcoin 2024 (Nashville)
At the Bitcoin 2024 conference Saylor forecasted that Bitcoin could reach $13 million per coin by 2045 (base case) and promoted aggressive BTC adoption strategies.
Exercised stock options; Bloomberg reports ~$400M windfall (Q1 2024)
Bloomberg reported Saylor exercised stock options that realized roughly $400 million in Q1 2024.
Settled D.C. tax dispute for $40M
In June 2024 Saylor agreed to settle the District of Columbia tax dispute by paying a $40 million fine.
MicroStrategy stock split 10:1
MicroStrategy completed a 10‑for‑1 stock split for both Class A and Class B shares (reported as impacting share counts and ownership percentages).
Reported ownership: ~19,998,580 Class B shares (~9.9% of outstanding; ~45% voting power)
SEC filings reported Saylor owned 19,998,580 Class B shares (about 9.9% of outstanding shares) with roughly 45% of voting power (post stock split adjustments).
Reported inventor on 48+ patents (site biography)
Michael.com's biography and later reporting credits Saylor as inventor on 48+ patents (growth of intellectual property portfolio).
Company rebranded from MicroStrategy to Strategy
MicroStrategy announced a corporate rebrand to Strategy (Feb 5, 2025), continuing its positioning as a corporate bitcoin‑holding / strategy company.
MicroStrategy holdings reported: 499,096 BTC ($27.95B at avg $62,473)
As of Feb 24, 2025 MicroStrategy reported owning 499,096 bitcoins acquired for $27.95 billion at an average price of $62,473 per bitcoin — reflecting massive corporate BTC accumulation.
Key Achievement Ages
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